Probing the effect of allylic substitution on cyclic ammonium ylid rearrangements

Sançon, J. and Sweeney, J. B. (2010) Probing the effect of allylic substitution on cyclic ammonium ylid rearrangements. Synlett, 2010 (4). pp. 664-666. ISSN 1437-2096 doi: 10.1055/s-0029-1219348

Abstract/Summary

The [2,3]-sigmatropic rearrangement of tetrahydropyridine-derived ammonium ylids is a valuable method for the preparation of substituted pyrrolidine carboxylates. The presence of an allylic substituent does not intrinsically reduce the yield of rearrangements, and the diastereoselectivity of rearrangement is related to the structure of the diazo reactant. The method represents a very rapid means of accessing complex pyrrolidines, as shown by preparation of a precursor to the core of lactacystin.